4-Methylmorpholine → HCID 10223065, compound

HRID 1935175Notes

Reaction equation

HRID 1935175 reaction equation
[C:1]([OH:6])(=O)/[CH:2]=[CH:3]/[CH3:4].ClC(OCC(C)C)=O.CN1CCOCC1.[NH2:22][C:23]1[CH:24]=[C:25]2[C:30](=[CH:31][CH:32]=1)[N:29]=[CH:28][C:27]([C:33]#[N:34])=[C:26]2[NH:35][C:36]1[CH:41]=[CH:40][CH:39]=[C:38]([Br:42])[CH:37]=1>C1COCC1>[Br:42][C:38]1[CH:37]=[C:36]([NH:35][C:26]2[C:25]3[C:30](=[CH:31][CH:32]=[C:23]([NH:22][C:1](=[O:6])/[CH:2]=[CH:3]/[CH3:4])[CH:24]=3)[N:29]=[CH:28][C:27]=2[C:33]#[N:34])[CH:41]=[CH:40][CH:39]=1

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 637090Crotonic AcidHCID 99677126-Amino-4-(3-bromophenylamino)quinoline-3-carbonitrile

Product 1

HCID 10223065HCID 10223065, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 0.637 g (7.40 mmol) of E-but-2-enoic acid in 25 mL of THF under N2 was chilled in ice. Isobutyl chloroformate (1.01 g, 7.40 mmol) and N-methylmorpholine (0.747 g, 7.40 mmol) were added and the solution was stirred cold for 10 min. A slurry of 1.00 g (2.96 mmol) of 6-amino-4-(3-bromophenylamino)quinoline-3-carbonitrile in 15 mL of THF was added and the mixture was stirred at 25° C. overnight. The mixture was evaporated and the residue was slurried in water, collected and dried. The residue was boiled twice with EtOAc and dried in vacuo (50° C.) to give 0.965 g of (E)-but-2-enoic acid [4-(3-bromophenylamino)-3-cyanoquinolin-6-yl]amide as a yellow solid: mass spectrum (electrospray, m/e): M+H 406.9, 408.9.

Workup

  1. stirringthe mixture was stirred at 25° C. overnight
  2. customThe mixture was evaporated
  3. customcollected
  4. customdried
  5. customdried in vacuo (50° C.)

Sources & evidence

ORD record
ord-04d326fa225f4997bab8bd57b691fe1a
Source dataset
uspto-grants-2002_05
Patent number
US06384051B1

Reaction notes

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